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pubmed-article:16018694rdf:typepubmed:Citationlld:pubmed
pubmed-article:16018694lifeskim:mentionsumls-concept:C1523814lld:lifeskim
pubmed-article:16018694lifeskim:mentionsumls-concept:C2603343lld:lifeskim
pubmed-article:16018694pubmed:issue15lld:pubmed
pubmed-article:16018694pubmed:dateCreated2005-7-15lld:pubmed
pubmed-article:16018694pubmed:abstractTextThe anion binding properties of fluorinated calix[n]pyrroles (n = 4-6) in aprotic solvents (acetonitrile and DMSO) and modified reaction conditions allowing for the synthesis and isolation of the hitherto missing dodecafluorocalix[6]pyrrole from the condensation of 3,4-difluoro-1H-pyrrole and acetone are described. In acetonitrile solution containing 2% water, the association constants for the 1:1 binding interaction between octafluorocalix[4]pyrrole and chloride anion obtained with isothermal titration calorimetry (ITC) and (1)H NMR titration methods were found to match reasonably well. As compared to its nonfluorinated congener, octafluorocalix[4]pyrrole was found to display enhanced binding affinities for several representative anions in pure acetonitrile as judged from ITC analyses. Similar analyses of the fluorinated calix[n]pyrroles revealed an increase in the relative affinity for bromide over chloride with increasing macrocycle size, as manifest in a decrease in the binding ratio K(a(Cl))/K(a(Br)). Anion binding studies in the solid state, involving single-crystal X-ray diffraction analyses of the chloride and acetate anion complexes of octafluorocalix[4]pyrrole and decafluorocalix[5]pyrrole, respectively, confirmed the expected hydrogen bond interactions between the pyrrolic NH protons and the bound anions.lld:pubmed
pubmed-article:16018694pubmed:languageenglld:pubmed
pubmed-article:16018694pubmed:journalhttp://linkedlifedata.com/r...lld:pubmed
pubmed-article:16018694pubmed:statusPubMed-not-MEDLINElld:pubmed
pubmed-article:16018694pubmed:monthJullld:pubmed
pubmed-article:16018694pubmed:issn0022-3263lld:pubmed
pubmed-article:16018694pubmed:authorpubmed-author:LynchVincent...lld:pubmed
pubmed-article:16018694pubmed:authorpubmed-author:SesslerJonath...lld:pubmed
pubmed-article:16018694pubmed:authorpubmed-author:ChoWon-SeobWSlld:pubmed
pubmed-article:16018694pubmed:authorpubmed-author:MarquezManuel...lld:pubmed
pubmed-article:16018694pubmed:authorpubmed-author:ShriverJames...lld:pubmed
pubmed-article:16018694pubmed:authorpubmed-author:GrossDustin...lld:pubmed
pubmed-article:16018694pubmed:issnTypePrintlld:pubmed
pubmed-article:16018694pubmed:day22lld:pubmed
pubmed-article:16018694pubmed:volume70lld:pubmed
pubmed-article:16018694pubmed:ownerNLMlld:pubmed
pubmed-article:16018694pubmed:authorsCompleteYlld:pubmed
pubmed-article:16018694pubmed:pagination5982-6lld:pubmed
pubmed-article:16018694pubmed:year2005lld:pubmed
pubmed-article:16018694pubmed:articleTitleAnion binding studies of fluorinated expanded calixpyrroles.lld:pubmed
pubmed-article:16018694pubmed:affiliationDepartment of Chemistry and Biochemistry, 1 University Station-A5300, The University of Texas at Austin, Austin, TX 78712-0165, USA. sessler@mail.utexas.edulld:pubmed
pubmed-article:16018694pubmed:publicationTypeJournal Articlelld:pubmed
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